


Should've Just Gone to Bed

by jensenisafallenangel



Category: Supernatural
Genre: Alcohol Abuse/Alcoholism, Alternate Universe - College/University, Angst with a Happy Ending, Benny Lafitte & Dean Winchester Friendship, Bisexual Dean, Brief Meg/Cas Dating, Coming Out, Dean Has Commitment Issues, Dean Hates Himself, Explicit Language, Explicit Sexual Content, F/F, F/M, Forgiveness, Gay Castiel, Jealous Dean, M/M, Minor Character Death, Misunderstandings, POV Dean Winchester, Past and Present, Roommates, Second Chances, Self-Acceptance, Songfic, True Love, Unhealthy Coping Mechanisms, Weddings
Language: English
Status: Completed
Published: 2015-11-24
Updated: 2016-02-22
Packaged: 2018-05-03 04:19:46
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 17,279
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5276366
Author URL: https://archiveofourown.org/users/jensenisafallenangel/pseuds/jensenisafallenangel
Summary: <blockquote class="userstuff">
              <p>When Dean gets really drunk, he calls his ex-boyfriend Castiel. The mornings after, Dean regrets it because of what happened between them in the past but what if he could be forgiven? </p><p>A story guided loosely by Plain White T's song of the same name.</p>
            </blockquote>





	1. Sam's Wedding & 8 Years Ago

THE WEDDING

 

Dean didn’t have that much to drink or at least that’s what he tried to believe. The slight stumble in his walk and definite slur to his words went largely unnoticed by everyone else since they also had plenty to drink. The polished dance floor spun under him slightly but Dean was determined to find Sam. He took each step carefully. 

Dean used the fact that his younger brother had gotten married as an excuse for his intoxication. 

“Sammy, co’mere,” Dean said, goofy grin on his face once he finally tracked him down in the big banquet hall. 

He pulled his brother under his arm, difficult since Sam was taller, and messed his hair with his other hand. 

“Ow,” Sam protested half-heartedly. He knew Dean wouldn’t let up.

The man had taken a very long time on his hair before his big day and Dean had already teased him mercilessly for it. 

“Didn’t hurt, don’t be a bitch,” Dean argued. 

“Jerk,” Sam replied good-naturedly. 

Dean kept drinking the whiskey from his glass.

“Dean, you sure you sh…”

“Don’t start, man,” Dean cut him off. “I’m good.”

“You sure?” Sam asked, feeling how heavily Dean was leaning on him now.

“I’m great. Just celebrating my baby brother getting hitched before me, no big deal.”

“Oh come on, you said it didn’t bother you!” Sam said indignantly. 

He had made sure to ask long before the wedding since they were four years apart and he didn’t want Dean to be upset. Dean hadn’t had a solid or lengthy relationship in years and Sam couldn’t wait and he didn’t want to, not for Jessica. He told everyone he knew he wanted to marry her after their first date four years ago during their freshman year at Stanford. 

“It doesn’t bother me,” Dean said, being mostly honest. 

He let go of Sam and wandered over to the bar and downed his whiskey before convincing everyone at the bar to take a shot with him. Sam shook his head and was grateful that his brother had already given his best man speech while decently sober. His older brother’s bowtie was askew and his short hair ruffled. The guy was a mess but Sam let him have his fun.

Dean didn’t have any more solid memories of the night after taking his shot.

 

Dean hadn’t had a worst morning after drinking since college, definitely in the top five of the worst mornings of his life. Before he could string any coherent thoughts together upon waking up, he spilled his stomach. He made it to the toilet, a very thin silver lining since he felt like death.

“Unnngh,” he groaned, knees digging painfully into the tile and elbows braced on the porcelain seat.

His head pounded and was only halfway sure where he was. Then he heard someone, a woman, from the other side of the door. 

“You okay?”

Dean took a second to collect himself before he could answer that. The little soaps and shampoos and excessive number of towels clued him into the fact that he crashed in a hotel, presumably the one where the wedding reception took place downstairs the night before. Okay. Dean could figure this out. 

The other person, though, Dean didn't know who…

The someone knocked on the bathroom door. 

“Dean, are you okay?” she called again. 

“I’m great,” Dean lied. 

“All right, well I have to take off but it was fun. Call me if you want to do it again sometime.”

“Sure…”

“It’s Shaylene. Seriously?”

Dean shrugged as he heard Shaylene leave and slam the bedroom door after she called him an asshole. He figured he wouldn’t see her again.

As he kneeled in front of the toilet, he attempted to piece together the previous night. He struggled with fuzzy bits and pieces, like trying to remember a dream.

When he felt a little better, he stood to drink some water from the sink then gripped the counter to stay standing. Gradually, the headache subsided enough that he could think a little more clearly. He tried to remember if he packed painkillers and he thought he might have. 

He remembered talking to Sam and joking about him getting married first even though it really didn’t bother him since Jess made him happy. That was all Dean wanted for his little brother. They took shots and then…

Now he could vaguely remember flirting and then dancing with Shaylene, one of Jess’s bridesmaids. He really should have known her name from the rehearsal dinners and everything else. After they danced, Dean suggested they come up to his room. Or she did. Whatever. 

Dean decided to take a shower and stepped right in since he lacked clothing. As he shampooed his hair with the hotel’s brand, another wave of nausea hit him but he held it together. He closed his eyes and let the water relax him. He kept relaxing until he recalled something.

There was a call…he called someone. Or got a call. He couldn’t exactly remember anything else so he needed to check his phone when he looked for the aspirin. 

He finished up in the shower and wrapped a plush white towel around his waist and stepped out of the bathroom. The spotless room connected to a spacious bedroom that had a door closing it off from the rest of the suite. 

Two people had clearly slept in the bed, a luxurious king. The condom wrapper and used condom in the garbage under the mahogany desk let Dean know he did in fact sleep with Shaylene. At least he used protection despite his hammered state. 

He found his phone in the pocket of his dress pants on the floor along with the rest of his clothes he wore to the wedding and reception. Of course, it had died. He remembered he had left his bag for the weekend on the other side of the bedroom door in the living room of the large suite. The day before got so busy he hadn’t really taken anything out of it

Charlie, his best friend, sat on the black leather couch drinking coffee when Dean walked out.

“Morning,” she said with her usual infectious smile.

“Hi,” Dean replied, allowing the redhead to be a cheerful morning person without complaint for once. 

Dean dug through his bag, found his charger and plugged his phone in.

“Morning,” came another woman’s voice.

Dean looked up and saw Gilda, a good-looking brunette and another of Jess’s bridesmaids.

“Hi,” Dean said before giving Charlie an impressed look. 

Charlie shrugged with a sheepish smile. Gilda’s eyes only focused on Charlie so Dean wasn’t embarrassed that he was only in a towel despite not knowing her. Charlie was like a little sister to Dean and it wouldn’t bother her. 

Dean turned his phone on and kept his eyes down as he heard Gilda say she had to go but gave Charlie her number and a kiss goodbye.

“Kudos to you,” Dean smirked once Gilda left.

“Thanks,” Charlie rolled her eyes and sat back down. “What did you do to piss off Shaylene so bad?”

“Forgot her name,” Dean admitted with a shrug. “Wasn’t the first time I’ve done it and it won’t be the last. Yesterday night is a little blurry.”

“That has to be an understatement,” Charlied laughed. “You were a hot mess, let me tell you.”

“Shit,” Dean cursed, his phone finally on and looking at the call history.

“What?” Charlie asked, walking over to him.

“I called Cas.”

“You don’t remember that?” 

“No. You do? What happened?” Dean needed to know. 

He tried hard to remember. Oh, this was not good. Not good at all.

“I was busy with Gilda, she was incredible, she can do this one thing with her…”

“Charlie,” Dean snapped. “Focus.”

“Testy,” Charlie replied, eyebrows raised. “Anyways, we were interrupted by you and big-tits coming in and I heard you tell Shaylene to go wait in the bedroom because you needed to call someone.”

“Ugh, fuck,” Dean groaned. 

He sat on the couch. Well, more like collapsed dramatically. It did his stomach no favors but a deep breath and closing his eyes helped the nausea subside a little.

“Relax,” Charlie tried, “I heard the conversation. It wasn’t…that bad.”

“You emphasized ‘that.’ Meaning it was still bad,” Dean pointed out, eyes snapping wide open.

Charlie looked away which Dean took as a yes to his guess.

“God damn it. What did I say, Charlie?”

“You sounded really drunk so I doubt he put much stock into it. You said how Sam was getting married and that you wished you had someone special. Then Cas said…” Charlie paused, trying to remember.

It hit Dean what Cas had said. The only thing that he clearly remembered from their conversation now was that Cas said, “You can’t just break my heart and then do this, Dean.” Then maybe he mentioned a relationship? Like he was in one? Wouldn’t that just be Dean’s luck, bother an ex who was married or engaged or something. 

All the thinking made Dean’s head hurt more.

He didn’t mention what he knew to Charlie.

“I don’t know what he said but then you said ‘hello’ a few times because I guess he hung up,” Charlie explained.

“Shit,” Dean said, falling back and hitting his head on the wall as he did so.

Charlie patted his shoulder reassuringly. Dean got struck by another wave of nausea that wasn’t necessarily from the alcohol. He hated his drunk self. 

“How can I fix this?” Dean asked.

“Maybe try to talk him sober?” Charlie tried.

“Oh come on,” Dean scoffed. “You know he hates me and you know why.”

“I do. But I also know you should try.”

Dean didn’t share her confidence. They had a complicated past and it was one he didn’t think anyone wanted to bring back up. He wished he didn’t call Cas at all. He should have just gone to bed. 

 

EIGHT YEARS AGO

Dean looked around with his mouth open a little. He couldn’t believe he carried a bunch of bags inside a dorm building, ready to start college.

“What a freshman,” some guy said as he walked passed with a buddy. They both laughed.

Dean closed his mouth and set his mouth in a hard line. They didn’t how hard he worked to get to this moment. 

After he checked in and got his room key, he went up to the fourth floor. His dorm room was about what he expected, simple and small, and vaguely reminiscent of a jail cell, which he knew from brief experience. The white walls weren’t helping the minimalist design flow.

“You must be my roommate,” Dean said as he noticed a guy putting stuff away in drawers of a dresser to the right.

“Name’s Crowley,” he stuck out a hand, “you must be Dean.”

“Yup,” Dean shook his hand.

They continued to unpack in silence. Dean almost mentioned that the dude must be hot in the August heat wearing a black suit that seemed way too formal but decided against it. Making an enemy of your roommate seemed like a bad way to start college. 

However, Dean had an immediately bad gut feeling about Crowley so he went to hang out on the floor’s lounge to try to meet more people. Unpacking didn’t take long since he didn’t have much. His family wasn’t what anyone would call rich by any means and he only had a few clothes and things to take with him from home.

Everyone must have still been in their rooms. Everyone except for the one guy who sat in the lounge reading a book. Dean didn't know if he wanted to try to talk to him since the nice clothes he wore suggested he was either a nerd or pretentious. Or both. He wore a frickin’ button-up shirt and dress pants. 

Dean didn’t understand the people he had met. Crowley dressed well, so did this guy, and Dean had a black t-shirt and jeans. Dean didn’t usually feel self-conscious but these guys didn’t help with their fancy stuff. 

The guy looked up and tilted his head to the side. Dean found it hard to believe how blue the guy’s eyes were. He had dark brown hair that made it look like he had just gotten up from a nap.

“Hey, sorry,” Dean started, “didn’t mean to just, you know, stand here like a weirdo…I’m Dean. I live in 405.”

“Hello, Dean,” the guy answered, his pink lips slightly turning up into a smile. “I’m Castiel. I’m in 409.”

“Cool.”

Dean paused. Normally, he excelled at talking to new people. He wasn’t sure why this guy was any different. Maybe it was those damn eyes staring at him. Dean cleared his throat when the silence got awkward. 

“Whatcha reading?” Dean asked.

“Slaughterhouse Five,” Castiel answered. “It’s for…”

“English 105?” Dean interrupted.

Castiel nodded.

“Awesome, I’m in in it too. I already read the book, couldn’t put the thing down,” Dean stopped, feeling a little wary about his excitement. He expected Castiel to judge him for getting into it.

“It’s really good so far, I agree,” Cas replied, smiling just a little. “When do you have the class?”

“Monday, Wednesday, Friday at 9. You?”

“Same. We could go together. Maybe discuss the book after I’m done reading it?”

“Yeah, I’d like that. I’ll let you get back to reading then. Nice to meet you, Cas.”

“You too, Dean.”

 

The two of them had that class together and a biology class as well. Both of them were trying to get their general education requirements out of the way early. Dean felt fortunate they had classes together at all due to the massive size of the University of Kansas. Dean didn’t know how he would have handled the big lecture halls full of freshmen without Cas. He was really glad he knew someone.

Dean majored in engineering and Cas double majored in anthropology and sociology. He told Dean he really liked studying people while Dean liked studying machines and for the most part found people crazy.

As for his roommate, Crowley wasn’t around much and Dean was almost too scared what he got up to in his spare time. Dean didn’t even know the guy’s major.

“Dude, seriously. He’s probably selling drugs,” Dean suggested. 

Dean and Cas studied in the library in late September. Dean got distracted easily and hated the library where everyone glared if he played his music too loud but Cas always dragged him along.

“Most likely,” Cas agreed. “Do your calculus.”

“You’re lucky your roommate had a mental breakdown and dropped out,” Dean grumbled before focusing on his homework. He didn’t see Cas look up briefly to smile at him before looking back down. 

As the year went on, Dean and Cas got closer. Dean could say with certainty that Cas was his best friend there. Dean only told Cas about his mom passing away a long time ago and how his dad struggled but always did his best for his boys. Dean even told Cas about his little brother, Sam, still in high school, who he called all the time and went home nearly every other weekend to visit since they were from Lawrence where the school was.

Cas stayed vague about his home life but seemed to be at school to get away from them. He didn’t go home for fall break and Dean felt bad leaving him on a basically empty campus but they weren’t that close at the time. 

For Thanksgiving, Dean invited Cas to come home with him because he wanted Cas to meet his dad and brother. Dean knew the holiday had a strong connection to family so he didn’t want Cas to avoid his and just stay at school alone. Cas agreed to meet the rest of the Winchesters.

Sam and Cas got along great right away. Their nerdiness helped them bond, Dean joked. John even seemed to soften up a bit. Cas also met Bobby, Ellen, Jo, and Ash who were family although not by blood. They always helped Sam and Dean with anything and had always made sure the boys were fed if John disappeared for a bit on one of his benders.

“What do you think, Cas? They’re not too embarrassing are they?” Dean asked. 

In Dean’s room, the smallest in the Winchester house since Dean let Sam take the slightly bigger one while John had the master, they talked while Cas laid in Dean’s twin bed and Dean politely took the floor so his guest would be comfortable. 

“They’re great, Dean,” Cas said. “I really like them. I see where you get the sullenness though, your father. Bobby clearly passed on a gruff attitude and Ellen is quite tough. I see why you would want to be like her, too.”

“All right, Dr. Phil,” Dean laughed. “Just wait until I meet your family and I can psychoanalyze all of your traits.”

Dean spoke without thinking but knew he touched a sore subject. He clearly hit a nerve since Cas didn’t answer. 

“Cas, I’m sorry. I didn’t…”

“It’s fine, Dean.”

“You sure? I know…”

“Really,” Cas answered. “Your family’s great. I’m glad I got to spend Thanksgiving with them.”

“Me too. Night, Cas.”

“Good night, Dean.”

Over Christmas, Cas went home to Chicago since his parents insisted he could grace them with his presence if they paid his tuition. Dean went home as well and didn’t mention meeting Cas’s family. They texted everyday over the break, even if only sending emojis back and forth. Since Dean had shown them to Cas, the guy couldn’t get enough of them.

Starting the second semester, Dean and Cas met a couple of new friends from their classes. They now had a guy from Louisiana named Benny and a girl named Meg who Dean forgot where she was from. Dean had class with Benny, another engineering major, and Cas had class with Meg. Dean and Cas didn’t have class together this semester but Cas still insisted he come to the library with him to study, keeping it their time to spend together.

Truth be told, Dean only tolerated Meg since Cas seemed to like her so much for a reason Dean didn’t get. He got close to Benny, already almost as close as he was to Cas. Benny and Cas seemed to not get along all the time and Benny and Meg rarely talked. Dean and Cas were the glue keeping the group together. 

 

“Why don’t you ask her out then?” Dean asked, a little angrily.

The two of them ate lunch in the cafeteria one day in March and Cas kept going on and on about something neat Meg had done. Dean had zoned out until he became sick of hearing about her. It bothered Dean that Cas seemed to like Meg so much, almost like jealousy but that wouldn’t make sense. Cas could be friends with or date whoever he wanted.

“I don’t understand why you’re upset, Dean,” Cas said. “I thought you would want to hear that Meg was picked to do research with a professor. It’s a big deal for a freshman.”

“Yeah, it’s great. Good for her,” Dean said, not hiding the sarcasm. 

Cas, usually not one for sarcasm, could read it loud and clear.

“Dean…”

“Seriously. Just ask her out,” Dean snapped.

Cas narrowed his eyes.

“Fine.”

Dean watched Cas get up and throw his half-eaten food out before storming out of the cafeteria. Not sure what to do about it, Dean finished eating alone even though he pretty much lost his appetite.

 _Why does it matter_ , Dean thought, _Cas is a single guy, he’s smart and attractive and…_

Hold up. Dean halted that train of thought right there. He did not have feelings for his best friend. His best _guy_ friend. 

But he couldn’t think of another reason why Cas asking out Meg bothered him so much.

 

Since Cas and Meg started dating off his own boneheaded advice, Dean felt miserable and he couldn’t forget his own stupid mouth brought them together. He didn’t see Cas that often and it had gotten tense between them. Dean tried a half-ass apology for snapping at him and spun a lie about being glad the two of them were together but things stayed awkward.

Meg couldn’t keep her hands off of Cas, constantly kissing and touching him, and Dean couldn’t hang out with both of them together. One day while avoiding them, he hung out with Benny and mentioned that it had gotten out of hand.

“You don’t like the PDA?” Benny asked.

“No,” Dean grumbled.

“You sure you’re not jealous, brother?” 

“Jealous? No, I wouldn’t want to date Meg!” Dean deflected.

“Not quite what I meant,” Benny said, with a knowing glance. 

He spoke quiet enough that Dean could pretend he didn’t hear and ignored him. They kept playing their video game killing monsters in a forest, working as a team. Dean appreciated that Benny didn’t push the subject further.

 

Over spring break, Dean told Sam all about what happened.

“So, you got jealous and now he’s dating someone else and you’re even more jealous?” Sam asked.

“What? No, that’s not what I said,” Dean replied defensively.

“Well, that’s what I heard. Why don’t you tell him?”

“Tell him what?”

“Tell Cas how you feel about him,” Sam shrugged.

“How I feel. Really, Sammy? You know I’m not gay,” Dean snapped.

“I know. I also know how you guys looked at each other at Thanksgiving,” Sam pointed out.

“Bite me,” Dean said eloquently. 

“You’re just mad because I’m right.”

He didn’t have an answer and let Sam scamper off without another word. 

Dean considered what Sam said. He and Cas had never discussed their preferences. But Cas knew Dean always went home with women at parties. Dean only got Cas to go to one party and Cas had gotten pissed when Dean left him there to get laid. Dean thought Cas only got mad because he left him but maybe he was jealous too. 

His feelings could be one-sided so Dean didn’t want to say anything. He and Cas planned on rooming together the following year and Dean didn’t want to ruin their now shaky friendship.


	2. 2 Months After the Wedding & New Year's 7 Years Ago

TWO MONTHS AFTER THE WEDDING

Dean lived in content bliss since Sam’s wedding and only occasionally thought about Cas and that stupid phone call. If by occasionally he meant every day. Instead of focusing on past dumb mistakes, Dean had kept busy with work.

Life as a firefighter was hard but Dean liked it a lot. Crappy hours didn’t matter to a single guy like him and he made enough to get by comfortably since he didn’t need much. He had grown up with less and kept a better lifestyle than ever before. On a good day fighting fires, he got to save lives and made sure kids got to grow up with both parents. Saving lives satisfied Dean but that wasn’t always the case.

After a particularly hard day that included an apartment fire and a couple lost lives, Dean felt like crap. A woman died who had had kids and Dean just thought of his own mother who died in a fire when he was four. He knew it certainly wasn’t his fault that this woman died but the guilt ate at him. He always wanted to save everybody.

When he got home, he skipped dinner and went right for the whiskey. Normally, he cracked open a few beers after work but he needed a little more to drown his thoughts. His captain had talked to the whole firehouse about talking to someone when shit was dark but Dean didn’t need the sob story therapy crap. Jack Daniels was the only therapist he needed.

His phone rang after a few gulps.

“Yeah,” he answered without bothering to check who called.

“You gonna let me in?” Charlie asked impatiently.

“What?” Dean answered, confused.

“Dean, it’s Wednesday? Dr. Sexy? How could you forget, we do this every week!”

“I’m sorry, Charlie. It was a really shitty day and…”

“Do you want me to go?” she replied. “We can watch another time.”

“No,” Dean said after a pause. “This will be a good distraction.”

“Awesome. Now let me up, I have a pizza that’s getting cold.”

Dean let Charlie up to his apartment. It was nothing special, just one bedroom, but nice enough and in a good part of town. It was close to work and he had a nice kitchen so he was happy. Happy with his apartment at least.

The two of them crashed on the well-worn black leather couch that by now had permanent indents of their butts. Dean flipped on Dr. Sexy, their shared guilty pleasure TV show. Charlie was a great friend, an amazing listener and fiercely loyal plus they could geek out over the same stuff. The show had hot people of all kinds and was hard to dislike in their minds. 

Dean switched to beer while they ate the half meat-covered, half veggie pizza but then he hit the whiskey again when they finished it.

“Really?” Charlie asked, one concerned eyebrow raised.

“Like I said,” Dean said before taking a drink. “Shitty day.”

Charlie opened her mouth to argue but a stern look from Dean kept her from nagging any further. She knew he had unhealthy drinking habits but didn’t know if she should step in. His relationships with friends and family didn’t suffer from his drinking and it didn’t affect his work. His apartment stayed nice and she knew he didn’t struggle financially because of his drinking so she kept her mouth shut. At least for the time being, she told herself.

The episode ended but they kept the news on as background noise and just chatted. Charlie had seen Gilda a few more times and it progressed well. Dean didn’t have anything to report since he didn’t want to talk about work and not much else went on in his life but he was glad one of his best friends was happy.

Dean’s phone rang again Dean’s phone rang again despite the late hour. Immediately, he panicked.

“Sam? Everything okay?” Dean asked, habit of fearing the worst kicking in.

Nothing like a late night phone call to create a panic and sober you up.

“What? Yeah! Everything’s great, more than great!” Sam said.

Dean could hear his smile over the phone. Relief sank in at his brother’s joyful words. He let out the breath he held.

“What’s up?” Dean asked, hoping he didn’t sound as drunk as he felt.

“Jess is pregnant! You’re going to be an uncle!” Sam exclaimed.

“No way! Pregnant? That’s…”

Dean got cut off by an excited scream from Charlie, who took the phone from Dean.

“Congratulations, you two!”

“Thanks, Charlie,” Sam said.

“Gimme that,” Dean grumbled and took his phone back. “Congrats, man. I’m really happy for you guys. We should go out and celebrate when your crazy boss gives you time off.”

“Oh, Lucifer’s not that bad.”

“Dude, his name is Lucifer,” Dean argued.

“Whatever. Get some sleep, Dean. I know you and Charlie party hard for Dr. Sexy,” Sam laughed.

“Bite me. And congrats again.”

“Thanks, Dean.”

Dean hung up and looked over at Charlie.

“Holy shit,” Dean said, before finishing his bottle of whiskey. “I’m gonna be an uncle.”

“Hurray!” Charlie grinned.

Dean forced a smile.

Charlie pointed out that it was late and she had to go. Dean showed her out and then went looking for more booze but he had run out.

Despite his happiness, Dean couldn’t ignore his obvious problem. He was jealous and, to be honest, a little bit lonely. Dean had always put Sam first but Sam didn’t need him to do that anymore. Sam had his own family and told Dean to worry about his own happiness but Dean didn’t know how to. He still felt like he needed to take care of Sam, his default top priority, so now he felt kind of useless. 

Two of Dean’s favorite people were happy and Dean tried to use that to make himself cheer up but he just couldn’t. A year had passed since his last relationship and he craved that connection again. 

As he fell back on the couch and glared at the whiskey bottle, blaming it for being empty, he tried to remember how full it was when he grabbed it. Probably over half. 

Dean’s stomach churned a little so he got up to get some water. It was never a good idea to bounce back and forth between beer and the hard stuff. He knew he would regret that in the morning, if not sooner.

 

The next morning, Dean woke up on his couch still in last night’s clothes. He downed the glass of water and aspirin on his coffee table that his drunk self left out. 

As sick as he felt from mixing beer and whiskey, he remembered everything from the night before. Hanging with Charlie, getting the call from Sam, calling Cas…

Fuck.

Dean sat upright on the couch too fast and nearly puked. 

“God damn it,” he said out loud to no one. 

He grabbed his phone that was almost dead off the coffee table. He definitely called Cas and the call was only a little over a minute.

Dean told Cas that Sam’s wife was pregnant. Cas tried to tell him to stop calling him but Dean cut him off. He remembered saying that he wanted to be happy and he asked Cas if he was happy with whoever he was with.

Cas had said he was. He was happy. He had moved on and Dean hadn't.

Damn it, he should’ve just gone to bed.

 

SEVEN YEARS AGO

Dean was nervous to start sophomore year. He and Cas were rooming together since they had set that up before arguing about Meg and neither had brought up switching roommates so the plan hadn't changed.

The two of them spoke sparingly over the summer. Dean didn’t know if Cas would even want to talk to him although he considered texting him about ten times a day. When they did talk, it felt more forced than when they used to talk and Cas didn’t use the emojis he liked so much. 

The two had a bigger room than the dorms they had freshman year and moved into a nicer and newer building. They had plenty of space for a futon Cas planned on bringing along with their bunked beds plus a fridge and microwave. They both had a medium sized dresser as well as a shared closet.

Dean had already moved in when Cas showed up. He read on the bottom bunk when he heard arguing down the hall. The arguing got closer and he recognized Cas’s voice and figured he was about to meet the Novaks. There were a lot of them by the sound of it. 

“I told you guys to be careful,” someone snapped as Cas opened the door.

“Hey Cas,” Dean grinned when Cas saw him.

He hadn’t realized how much he had missed his best friend until he saw him.

“Hello, Dean,” Cas answered.

His mouth turned in a small smile, barely there, but he didn’t seem upset with Dean.

A flurry of movement began. Two of Cas’s brother’s dragged the futon in while their father barked orders. Their mother told Cas’s sister where to put a couple of duffle bags and reminded Cas to hang up his nicer clothes right away. Order after order came and it made Dean’s head spin.

“Dean and I can put together the futon, you guys can go,” Cas said.

“That’s it, no thank you?” his father asked with a hard look in his eyes.

“Thank you. We can take it from here. I’ll see you at Christmas,” Cas said, shuffling his family towards the door after a rush of goodbyes.

“Now you know why I don’t go home for Thanksgiving. Can you imagine them trying to make a meal together?” Cas said. 

Dean laughed. “It’s good to see you, man.”

“You too,” Cas said, the small smile back again. “What do you say we build this futon?”

It took an hour and some good-hearted joking from Dean about Cas’s handyman skills but they got the futon built. The two of them sat on it together.

“You gonna see Meg?” Dean asked innocently enough.

Cas’s face fell slightly. 

“We broke up,” Cas said, dropping his eyes to the ground. 

“Oh,” Dean said. “How come?”

Dean tried to not smile. He felt irrationally happy that he would hopefully be free of Meg now. He told himself Cas being single had nothing to do with it.

“She broke up with me because I think she got bored of me.” 

“Bored? That’s bullshit, you’re not boring at all!” 

“Thank you, Dean,” Cas smiled. 

Dean thought about what to say and figured he should ask if Cas was okay.

“You doin’ all right?” Dean asked.

“I am. Being with her helped me realize something.”

“What’s that?”

“I’m gay.”

Dean didn’t really know how to respond to that and just kind of stared at Cas and kind of felt his mouth drop a little. Cas never seemed all that interested in women but he was all of a sudden very forward with the information. 

“Oh. You, uh, you never said that you…might, you know, be…”

“It never came up,” Cas shrugged. “Now it has.”

Dean nodded. He could have brought up a newfound curiosity he had in his own sexuality but he kept the focus on Cas.

“How come you dated her?” Dean asked.

“When we fought and you told me to…I guess I kind of overreacted and actually asked her out,” Cas admitted.

They shared a laugh at how ridiculous they had acted.

“You’re…okay with this?” Cas asked, concern obvious in his voice and on his face.

“Of course,” Dean answered, sure to look Cas directly in his eyes, “it’s who you are.”

Cas smiled, bigger than maybe Dean had ever seen him smile, and Dean couldn’t help but smile back.

 

The beginning of sophomore year had harder classes but Dean stayed on top of them thanks to Cas. He dragged Dean to the library and Dean grumbled like he used to and would still throw wadded up pieces of paper at Cas when he got bored.

For the most part, they got along great without Meg. Dean enjoyed having his best friend back and continued to repress any stronger feelings he might have for Cas to avoid messing up their friendship again.

Dean still regularly hung out with Benny. They kept playing their video game fighting monsters together in the forest. Since there were a lot of engineering majors and classes at the school, they only had one class together. 

“So, how’s Cas?” Benny asked as they played.

“Aw come on Benny, don’t pretend that you care,” Dean retorted as he cut the head off of some nasty thing.

“I don’t but you do,” Benny laughed.

“Oh this again? Jesus, we’re just friends.”

Dean kept his eyes on the game as Benny laughed some more.

“He did tell me he’s gay, though,” Dean said, eyes still on the game. “But I don’t know if he wants everyone knowing so don’t tell anyone.”

“You got it,” Benny agreed. “Now you know you could have a chance.”

Dean rolled his eyes.

“Even if I did want… that… it wouldn’t matter. My old man…”

“Doesn’t matter.”

“What?” Dean asked.

“It don’t matter what he thinks, brother. If you like him, go get him.”

They kept playing, now in silence. Dean’s character on screen died because he didn't pay attention and they started over without question. Dean tried to focus but his mind wouldn’t shut up.

Sure, his dad had never spoke against anything or anyone gay but he had never seemed too supportive of it either. A former Marine, Dean knew they weren’t known for being particularly tolerant. John always talked about Dean bringing a girl home from school and other crap like that so Dean figured there was no room for change in his dad’s vision for him. Wife, settle down, two and a half kids, all that…

“Shit,” Benny cursed as Dean’s character in the game died again.

“Sorry, Benny. Been a long day, I should get going.”

“All right,” Benny agreed. “I’ll see you in class tomorrow.”

“See ya,” Dean said, standing up to go. 

At the door, Dean added, “Thanks Benny.”

“For what?”

“Just… thanks.”

 

Dean invited Cas back home for New Year’s and he tried to build up the courage to admit his feelings to Cas once he could admit them to himself. Dean valued the heck out of their friendship but maybe something more would be even better.

For extra moral support, Dean invited Benny as well. Even though the two of them didn’t always get along, Dean hoped his friends could put aside their differences for the New Year.

The Roadhouse that Ellen owned and Jo and Ash worked at threw their annual party. The Winchesters had gone for as long as Dean could remember. He remembered sneaking off with Jo last year to break into the back room to steal some alcohol and getting caught by an irate Ellen. Dean had been eighteen and Jo was only fifteen. John had been too drunk to give a damn at the time but got pissed when he found out later.

Cas and Benny showed up the same day, on New Year’s Eve, at the Winchester house. Sam seemed to take after Cas and didn’t hit it off with Benny. John had hit the sauce early and mumbled a hello from the couch.

Later, at the party, Jo and Ash talked to Cas but left him to ask Ellen about something. Sam nudged Dean and pointed down at his watch showing the year had an hour left. Dean had to hurry if he wanted to come clean to Cas. 

“Cas, buddy, can I talk to you?”

Dean got Cas alone with time winding down.

“Sure, Dean. You know I always enjoy talking to you,” Cas said, lips turning slightly in a smile. 

“Well, I know we’ve been friends for over a year, you’re like my best friend, and I don’t want…don’t want anything to get ruined, ya know?” Dean started.

Cas’s face scrunched in confusion and he tilted his head a little.

“Dean, what are you talking about? What’s going to get ruined?” Cas asked.

“Hopefully nothing. I’ve been wanting to tell you something but I…I…”

Dean scratched at the back of his neck and looked over Cas’s shoulder for a second. Benny and Sam nodded and gave him a thumbs up. Despite the two of them not getting along, they both cheered Dean on and gave him the confidence he needed.

“Ten…nine…eight…” everyone in the bar started counting down.

“Dean, you’re kind of freaking me out,” Cas said.

“Five… four… three…”

Dean figured he could just show Cas what he meant instead.

“Two…one! HAPPY NEW YEAR!”

At that, Dean pulled Cas in by the lapels of his suit jacket and gently brought their mouths together. Dean stopped after a couple seconds to pull back and see Cas’s reaction.

Cas smiled and kissed him back. He tasted a little like root beer and it felt great for both of their first kisses with another guy.

The two of them kissed until Ellen told them to get a room.

“Happy New Year, Dean.”

“Happy New Year, Cas.”


	3. Traitors & Sophomore Year Dating

**Notes for the Chapter:**

> Finally some smut. It's at the very end if you want to skip ahead.

ONE WEEK AFTER THE PREGNANCY ANNOUNCEMENT 

 

Dean struggled along, continuing to put fires out and hearing good news from Charlie and Sam about their lives. He continued to drink more than healthy amounts but now turned his phone off when he started. He didn't want to keep bothering Cas. He didn’t want to keep bothering someone who had left his life a long time ago. Dean couldn’t ruin his happiness, again, due to his own loneliness.

Sam called Dean to meet for lunch. Dean thought they would finally celebrate Jess’s pregnancy but Charlie joined them. As much as he loved both of their company, their faces seemed anxious and put Dean on edge. He immediately assumed the worst.

“What’s up guys?” Dean asked, more than a little concerned.

“We’re worried about you,” Sam started.

“What is this, a fucking intervention?” Dean snapped.

A couple heads near their table turned and Sam gave him his signature bitch face while Dean glared. He couldn’t believe two of his favorite people turned on him. 

“No, not an intervention,” Charlie tried, “but we do want to help you.”

“Help me? Help me what?”

“Dean, we want you to be happy. So we want to know if there’s anything we can do to help. That’s it,” Sam explained.

“I am happy,” Dean shrugged, avoiding their eyes by looking at the menu.

“You go to work, come home and drink half a fifth with the company of only a turned off phone so you don’t call…you know… and that’s happy?” Charlie accused.

“Well, we don’t all need a relationship to be happy,” Dean argued.

He gave each of them one final glare and stormed out of the diner. 

Inside the diner, Charlie and Sam shared a worried glance.

“Who is he trying not to call when he drinks?” Sam asked.

“Who do you think?”

“Cas?” Sam guessed. 

Charlie nodded.

“I figured. You know, I think he’s the only person Dean ever really loved,” Sam mentioned.

“I think you’re right,” Charlie agreed.

“We need to get them back together,” Sam suggested.

“Even after what happened between them?”

Sam shrugged it off.

“It’s been a long time,” Sam reasoned.

“What if he’s dating someone or married?” Charlie pointed out.

“Details. Dean and Cas are meant to be together. You in?”

“You know it!”

 

Dean ignored the phone calls and texts from Sam and Charlie for the rest of the day. He decided to give a Benny a call. The man had moved back to Louisiana live near his family after college the last time Dean had talked to him. 

“Dean Winchester! How’s it going, brother? It’s been a few years,” Benny greeted.

“It has been, yeah. I just wanted to catch up real quick, see how you were doing,” Dean said. 

It was great to hear his old friend’s voice and he should have done this sooner.

“Real good. The whole engineering thing didn’t pan out so I opened a restaurant with Andrea.”

“Andrea?”

“My girlfriend. You should meet her sometime, Dean. She’s something special.”

“I’d love to.”

“What about you, working? Dating?” Benny asked.

“Still a fireman, which ain’t too bad. I guess neither of us were meant to be engineers, huh?” Dean joked. He specifically ignored the second question.

“Guess not,” Benny laughed. “Listen, I gotta run, lunch rush and all, but we should get together soon.”

“You got it, Benny,” Dean agreed.

“Still in Cali?”

“I am but we’ll make it work,” Dean figured.

“See ya, Dean.”

A friendly voice that didn’t piss him off or meddle in his life felt nice. He had missed Benny. Thinking of him brought back college memories and memories of…

Dean started to drink early.

 

Back at the law office Sam worked at, he kept pondering how to find Cas and get him to California. 

“Winchester, we don’t pay you to daydream,” a voice interrupted.

“I’m sorry. I’m worried about my brother,” Sam said. “Actually, there might be a way you can help.”

Lucifer grinned, knowing it would mean Sam would owe him a favor.

 

SIX YEARS AGO

 

After their kiss on New Year’s Eve, Dean and Cas started dating. Ellen, Jo and Ash admitted they already thought the two of them were dating at Thanksgiving and laughed before congratulating them. Bobby grumbled something sappy about being proud of Dean.

With a lot of Sam’s help and convincing, Dean planned on telling John when he went home one weekend in late February. Dean tried to visit home as much as he used to but it became harder to leave campus now that he dated Cas. For this, though, Dean didn’t want Cas to be there in case John reacted unpleasantly. Dean still struggled with the fact that he was dating a guy and he really didn’t want this to complicate things. But, John was his dad and should know.

“Dad, there’s something I have to tell you,” Dean said. 

Sam was in his room but surely eavesdropping. Dean was on the couch in the living room sharing a beer with his dad.

“What is it, Dean?” John asked, eyes not leaving the T.V.

“I’m, uh, dating someone.”

“That’s great! When can I meet her?” John asked, turning to look at his son.

“Well, you have met them,” Dean paused, nervously scratching the back of his neck. 

John seemed confused, probably because the only person from school that he had met was…

“Wait, you don’t mean…”

“Yeah. I’m dating Cas,” Dean announced. 

The idea of telling his father terrified him but he liked saying that he and Cas were dating. It still hadn’t gotten old after almost two months together.

“Really. I didn’t know you were gay,” John said, voice unnervingly steady.

“I’m not, I just…with Cas, I don’t know…”

“Well, son of a bitch. I never would have guessed but hell, if you’re happy…”

“You’re not mad?” Dean asked, confused.

“Mad? Not if my son is happy, then do whatever or whoever you want.”

“I kind of expected more of a fight.”

“When I was about your age and dating your mother, her father hated me. It was just so unnecessary and I know from experience it wouldn’t stop you even if I wasn’t happy,” John explained.

“Well, shit. Thanks, Dad.”

“Bring him around for dinner the next time you come home.”

“You got it.”

 

“How’d it go, did you tell him?” Cas asked when Dean got back to their dorm room Sunday afternoon.

“I did,” Dean grinned, “and he was surprisingly okay with it. He wants you to come to dinner.”

“So, both of our families know. That makes us official now,” Cas said, grin matching Dean’s.

Cas had told his family, somewhat reluctantly, and it went over like a ton of bricks. Apparently, they thought the gay thing was a phase and claimed they knew sending him far away was a bad idea although Cas fought them on it since he needed the space. Kansas was as far away as his parents would allow and Cas, dependent on them for tuition, had to comply and not go further away. 

“Well, what isn’t official is this futon. We built it and haven’t even broken in it properly,” Dean smirked.

He kissed Cas while he let him think of the implications of what he said.

“At least buy me dinner first,” Cas joked as Dean trailed kisses down his neck.

“Yeah, all right,” Dean agreed, mouth still on Cas’s neck.

Cas got Dean to stop just long enough to get their shoes on and head out the door. Dean kept touching Cas at least a little the whole drive there, holding hands, or a hand on Cas’s back as they walked into the restaurant. 

It maybe wasn’t the place but they discussed their plan for the evening.

“I’ve never really been in a relationship,” Cas admitted, moving his food around his plate.

“I’ve never been in one that was this great,” Dean smiled.

That reassured Cas who looked up and smiled. It had only been a couple months but it felt better than anything Dean had before.

“Is it weird that we’re discussing this in a restaurant?” Cas asked.

“Probably,” Dean laughed.

“I’ve never, uh…you know,” Cas said, nervous again.

“Well, I never have with a guy if that makes you feel better,” Dean tried.

“A little, yeah,” Cas said. “But what if I’m not any good?”

“We’ve done plenty already and you were great,” Dean reassured him.

Cas smiled a little bit again at that.

“Look, we can do what we’ve done before and if we want, we can go a little further. If we don’t want to then we don’t have to. Sound good?” Dean said, taking Cas’s hand on top of the table. 

“Sure,” Cas agreed.

 

Back at their room after dinner, they started like they always did. Making out on the futon, slowly grinding against one another and losing layers of clothes. Soon, they were both half-hard in just their jeans and boxers.

“You want to keep going?” Dean asked, hand dropping to Cas’s fly.

“Yes,” Cas said, a little out of breath already.

They got their jeans off and Dean teased Cas by rubbing him over his boxers.

“Dean, please.”

With a satisfied smirk, Dean quickly tossed Cas’s boxers out of the way and got back to work, stroking him to get him completely hard.

“You too,” Cas said, tugging at Dean’s boxers.

“Fair’s fair,” Dean agreed, throwing them on the floor.

Dean leaned down to kiss Cas again, their erections pressing together. Cas was lost in that and didn’t notice Dean grab lube while they were kissing.

“Did you stash that under the futon?” Cas asked.

“I figured we’d need to be prepared if we were, ya know, in the moment…”

“Dean. Stop talking and fuck me.”

“You’re sure?” Dean asked, holding off on how hot that was for a second.

“Yes,” Cas said in a needy whine.

Dean set to work slowly. He had maybe done a bit of research when he and Cas had started fooling around with handjobs and blowjobs to be sure about what to do. He took his time with each finger, stretching and watching Cas. Dean would occasionally lean down to kiss Cas and when he was three fingers in, got his mouth on Cas’s cock.

“Shit,” Cas cursed, back arching. 

Dean could tell Cas was close and stopped. Cas, breathing hard, watched Dean roll a condom on and slick himself with more lube. He was above Cas, lined up and ready.

“Cas, you good?”

“I’d be better if you started fucking me,” Cas complained.

Dean let out a laugh and kissed Cas.

“So needy,” Dean joked.

Dean very slowly entered Cas and let out a shuddering breath when he was fully seated. 

“Fuck, feel so good,” he groaned low into Cas’s ear.

Cas, in response, wiggled his hips just a little to hint to Dean to get moving. Gently, Dean pulled out and eased back in.

“I’m not going to break,” Cas teased.

Dean laughed again before quickening his pace just a little. He would never tire of seeing Cas’s face when they did stuff like this, seemingly in awe of Dean and he made the most maddening sounds. Dean figured he could come from just those moans and the way he groaned his name. 

He finally got a rhythm going and slammed into Cas who was groaning Dean’s name like he knew he liked.

There was banging on the wall from next door but Dean didn’t stop and Cas didn’t ask him to. Instead, Dean changed his position to hit that sweet spot and made Cas cry out in surprise. 

“Oh come on!” next door yelled.

Dean and Cas both laughed.

“He deserves listening to this, he’s an ass,” Dean said.

He kissed Cas, without faltering his pace, and somehow pounded into Cas even harder.

“Gonna…fuck, gonna…”

“Me too, angel. Right there with you,” Dean said back, face tucked into the crook of Cas’s neck.

Cas dug his nails into Dean’s back and came, untouched, while Dean kept going. Dean fucked him through his orgasm and followed closely and Cas could feel Dean come.

They took a moment to come down before lazily kissing for a bit. Dean figured Cas would want to clean the come off his stomach and got up to get a towel and throw out the condom. 

Once they were cleaned up, Dean flattened the futon so they could lay side by side comfortably. He threw a blanket over himself and Cas so they’d be warm since neither felt like putting clothes on.

“You doing all right, Cas?” Dean asked, pulling him against his chest and kissing below his ear.

“I am,” Cas answered. “You…you’re pretty good at that.”

“You’re not so bad yourself,” Dean replied as Cas backed his ass up against his dick.

“Good night, Dean.”

“Night, Cas.”

They began a lot of nights curled up together on the futon and the only way Dean slept soundly without alcohol was with Cas in his arms.


	4. After the Intervention/Junior Year

ONE WEEK AFTER THE INTERVENTION

 

Sam tried hard not to tell Dean his good news. After the failed intervention, Sam talked to Lucifer. Sam now had a way to track Castiel down and hopefully get him back together with Dean. 

Back when Sam got his job, he and Lucifer spent time getting to know each other even though Sam found his boss unnerving to say the least. Sam and Lucifer got to drinking one night and he learned that Lucifer had become estranged from his family. Long story short, Sam found out that Lucifer was Castiel’s cousin. He still kept tabs on them and knew where to find Cas. 

“Keep your enemies close and all that,” were Lucifer’s words. 

The information finally proved beneficial and Sam asked Lucifer how to contact Cas.

Sam had known the whole time about his boss’s connection to his brother’s ex-boyfriend but didn’t want to tell Dean originally because he figured that would just bring up the past and it would hurt him. Dean had opened up to Charlie and Sam about what had happened between him and Cas but after a lot of persistence. After he got drunk and spilled, no one brought it up again. At least, not until his drinking and loneliness had gotten out of hand. 

Sam knew what went down between Dean and Cas would make reconciliation a long shot but he had to try. He knew he found true love with Jess because she gave him the same looks Dean and Cas used to share. Sam learned what love looked like from them and he wouldn’t give up on that.

Sam needed Charlie on board as another mastermind to the plan.

“You know I’m all for true love and big romantic gestures, kissing in the rain and all that jazz,” Charlie started.

“But?” Sam asked.

“But I’m just worried we’re meddling too much and Dean will be pissed we didn’t let the past stay in the past.”

“He’ll be more pissed at me than you if this goes south, trust me,” Sam reassured her.

Sam and Charlie had a way to get Cas and Dean to meet up after all this time. Lucifer, in return for the crucial information, made it clear he would need something from Sam but he figured he could worry about that later. He and Charlie needed this to work and they needed to do it soon. Dean, ideally, would thank them. 

 

 

“Okay, you’re being weird,” Dean pointed out. “What’s up?”

Sam played it off like no big deal as they ate the next day at a diner. Dean had pretty much forgiven Sam for the intervention attempt and, to his credit, had tried to cut back his drinking a little. Deep down, Dean knew his brother and Charlie tried to help even if he didn't admit that out loud. 

They had a surefire way to make Dean happy and that was all Sam wanted out of his scheme.

“So, coffee tomorrow?” Sam asked as they left the diner and were going their separate ways.

“Sure,” Dean agreed.

 

FIVE YEARS AGO

 

Dean woke up with Cas in his arms like he had grown accustomed to. Both of them stayed on campus over the summer between sophomore and junior years to work. They started renting an apartment together and kept it, now partway through junior year. Dean worked as a mechanic on top of school while Cas focused more on school, only volunteering weekends at the museum he worked at over the summer.

It scared Dean how quickly he had become comfortable with Cas. They had a routine like an old married couple and bickered good-naturedly like one too. They had regular restaurants and argued about movie, T.V and music but always would watch and listen to what the other liked eventually. Somehow, Dean felt like he had known Cas forever, not just a couple quick years. 

Cas stirred a little in Dean’s arms and moved his ass against Dean’s dick in just the right way to get him going.

“Don’t start something you’re not going to finish,” Dean said into Cas’s ear.

Cas’s answer was to press and move even more, getting Dean to groan loudly.

“An apartment gives us a lot more space,” Cas said, turning to face Dean, “we can be much louder than last year.”

“Absolutely,” Dean grinned.

He let Cas climb on top and kept kissing him. Even if he struggled at relationships, morning sex Dean could do.

Cas took control, rolling his hips against Dean. Both were still naked from the night before and getting hard fast.

He kissed down Dean’s chest and stomach and stroked him a few times before sucking him down in one go.

“Fuck,” Dean said, barely more than an exhale of breath, “what a way to wake up.” 

Cas had gotten really good at this and had Dean coming in just a few minutes. He crawled back up to kiss Dean who didn’t mind tasting himself on Cas’s tongue. 

“You want me to return the favor, babe?” Dean asked, knowing he also had a knack for it.

“I have to go to class. And you’ll be late for work before your classes,” Cas said, kissing him again. “But tonight we have all the time in the world when we get back from dinner.”

“Dinner?” Dean questioned.

“Yes,” Cas rolled his eyes. “Our double date. We’re celebrating their engagement, remember?”

“Right,” Dean agreed. “I’ll meet you there when my class is done.”

“See you tonight,” Cas said. 

Dean lay in bed a minute longer and remembered their friends Hannah and Victor had gotten engaged and Dean had to act happy for them. Not completely act but they had dated for as long as Dean and Cas so it put the pressure on. Dean didn’t know if Cas expected a proposal and he didn't know how to bring it up.

An engagement felt huge and made Dean panic. If he and Cas ever got engaged, Dean didn’t know where they would live after school or how they would pay for things or if Cas wanted kids. Dean had thought about kids but didn’t know what he had to offer a child. Or Cas for that matter. Dean went to work with the intent for some classic cars to clear his mind.

No such luck. 

He couldn't focus, dropping things and bumping his head, and he barely took any notes in class. Dean worried he and Cas were getting too serious. They lived together, did everything together and went to celebrate friends’ engagements now. Dean couldn’t help it, he felt trapped. Suffocated. 

Instead of talking to Cas about it and how he felt, he went to a bar after his last class. He killed an hour before Cas found him. Dean, drunk enough to go without a fight, let Cas drive them home in the Impala. Dean didn’t bother making any excuses for missing dinner.

Cas didn’t waste his breath arguing with a drunk Dean since he knew better from experience. He kept his mouth shut and simply threw his boyfriend on the couch before slamming the bedroom door shut.

 

The next morning, Dean woke up by a serious need to puke. He made it to the bathroom just in time before emptying the entirety of his stomach. Skipping dinner was a shitty idea in more ways than one.

He brushed his teeth before he went back to the couch with a glass of water to wash down some aspirin. The amount of alcohol he had last night, while a lot, didn't erase his memory. Seared into his brain was a very angry Cas.

Of course, the noise from Dean throwing up woke Cas up and Dean braced himself for impact. While they didn’t fight often, Cas became a force to be reckoned with when they did. 

Dean didn’t lift his head as Cas came out of their room and sat on the coffee table in front of him. He didn’t even know how to start his apology.

“Cas…”

“You need to be able to talk to me, Dean,” Cas said, lifting Dean’s head gently with a hand under his chin. “Whatever you’re thinking, I’m here for you.”

“I know,” Dean agreed. “That’s not the problem.”

“Then what is?” 

Cas remained patient and levelheaded even when Dean pissed him off. Dean didn’t understand how he could he love someone so rash and hotheaded. It didn’t add up

“I just panicked,” Dean admitted, surprised at his own honesty. 

Cas waited for him to continue.

“I couldn’t…deal. Couldn’t face the fact that we’re like them, could be like them. I just don’t see you settling for me and…”

“Hey,” Cas said sharply, now gripping Dean’s face in his hands. 

Dean looked into his boyfriend’s blue eyes, somehow filled with admiration.

“I would not be settling for you, Dean Winchester. I love you. Just the way are. And I always will.”

“I love you too, Cas.”


	5. Reunion/What Happened 5 Years Ago Pt. 1

TWO DAYS AFTER SAM TALKED TO LUCIFER, ONE DAY AFTER SAM TALKED TO DEAN

 

Dean didn’t arrive late. He managed to show up early, an uncommon feat for him. He didn’t know why his brother already sat inside the coffee shop talking to someone. Sam sat at a table facing towards the door across from a guy whose back was to Dean. 

He walked towards them, figuring the well-dressed guy was a lawyer buddy of Sam’s. 

“Oh hey,” Sam greeted, seeing Dean.

The other man turned around. Dean certainly did not expect to see…

“Cas.”

Dean could feel his chest constrict after he managed the one syllable. He hadn’t seen Cas in five years and now all of a sudden here he was. The only person he had ever loved and the one person he had hurt the most. It could only be a God awful dream, maybe he drank too much again…

“Dean?” Cas asked.

Cas scrunched his eyebrows in confusion. His eyes were more beautiful than Dean remembered.

“Sam, what the fuck?” Dean glared.

This plan had Sam’s interference all over it and Dean didn’t appreciate the shock. It was hard enough trying to get over Cas without having him right in his face without warning.

“I think you guys have a lot to talk about so I’ll just go,” Sam said, standing up. “I got you a coffee, Dean.”

Dean couldn’t form angry enough words to convey the betrayal he felt from his brother going behind his back so he stayed quiet. One coffee wouldn't be enough for Dean to forgive him.

“Would you like to sit?” Cas asked, bringing Dean back to reality.

Dean felt nervous and unsure and must have looked it.

“If we’re both here, we might as well talk,” Cas said with a small shrug.

“Uh,” Dean replied lamely, “sure.”

Dean sat at the table across from Cas who didn’t look or sound as angry as he should be. Sam pulled a shitty stunt but Dean was no better. 

He looked down at the cup Sam left him. The markings on it said black coffee.

“I didn’t take Sam for the type to drink black coffee,” Cas said. “You on the other hand…”

Dean looked up and saw a small smile on Cas’s face, one that didn’t quite reach his eyes. A smile reminiscent of a better time, when Cas would wake up before Dean and bring him a cup of black coffee to get him up and going.

“I…” Dean started, not sure where to begin apologizing. “I didn’t know Sam was doing this, I thought he and I were just meeting for coffee.”

“I know,” Cas said, “your face was genuinely surprised to see me.”

“It’s been a while,” Dean said, one side of his mouth playing at part of a smile.

“Five years,” Cas stated matter-of-factly.

Dean awkwardly rubbed at the back of his neck.

“How, uh, how’ve you been?” Dean asked.

He didn't know how to proceed besides small talk so they could avoid touchier subjects like what happened all those years ago or Dean’s recent phone calls.

“Good. I’ve been teaching, that’s why I’m in California. There’s a conference,” Cas answered.

“You teaching anthropology and sociology?” Dean asked, remembering Cas’s passions.

“That and writing. I’ve published several textbooks,” Cas said.

“That’s good. Good for you,” Dean replied genuinely. 

“And you?” Cas asked.

“A fireman,” Dean said, feeling inferior to the successful professor. “Engineering didn’t quite work out.”

“You get to save lives,” Cas said, sounding impressed. “That’s incredible.”

Dean shrugged and drank some of his coffee. 

“What else have you been up to?” Cas asked, keeping the conversation going.

Dean couldn’t believe Cas didn’t scream at him or storm out. He acted more civil than Dean deserved but then again he always was the better person.

“I’ve just been helping Sam and Jess get ready for the baby,” Dean said.

Dean cringed a little as he remembered the night he told Cas. 

“Right. You said on the phone,” Cas said, crossing his arms across his chest.

Dean tried to read Cas’s expression but found nothing, not the anger he expected to finally come out or anything. Five years ago, they knew each other so well and practically read each other’s minds. This Cas was a stranger.

“Cas, I’m sorry about…all that. Those calls. I was just going through some shit and…”

“Then you go see a therapist.”

Dean could feel Cas’s anger. The façade from a couple minutes ago disappeared. Dean could read this face with no trouble. 

“I should have never called you. I should’ve listened to my head when it said leave it alone. But I was still trying to get over you and everything with Sam just made that hard.”

“You think maybe it was hard for me too?” Cas said, voice a little raised.

A couple heads turned and Dean anticipated a scene even though neither of them wanted that. A lot of built up tension after five years came out and a big blow-out would be difficult to stop.

“Cas…”

“I was trying to move on, start a life. And then you keep calling and bringing me back to that night…”

“I’m sorry, I know…”

“No, you don’t know!” Cas snapped.

He glared at Dean who didn’t what else to say. For all the times he had imagined being reunited with Cas, this picture didn't match up.

“I never wanted to hurt you,” Dean said, not being able to look up.

“Well, bang up job of that,” Cas stood.

“Cas,” Dean looked up, pleading as much as he could with that syllable. 

“Goodbye, Dean,” Cas said with biting finality. 

 

 

WHAT HAPPENED FIVE YEARS AGO PART 1

Dean had tried talking to Cas more, to open up and be honest and it almost worked. Junior year stressed Dean out. He didn’t snap at Cas or take his frustrations out on him but he didn’t always talk to him about what ate at him either. 

Cas focused on school but Dean had to balance work and school to afford everything. Earlier that year when they fought about paying bills, rent and groceries, Cas had offered to take more than his fair share since his parents paid for pretty much everything. That had resulted in a bit of a fight since Dean insisted he could take care of his half and he didn’t need charity.

“So, what do you want to do tonight?” Cas asked Dean, arms sliding around his shoulders.

Dean sat at their table working on homework and didn’t feel like doing anything except for finishing it. He took a deep breath before he answered. 

“Uh, whatever you want to do,” Dean said, distracted.

Cas stepped back and crossed his arms. Dean looked up from his homework.

“What?” Dean asked. 

“Nothing. We can get pizza and stay in. I know you have a lot to work on,” Cas shrugged.

Dean couldn’t tell if Cas was upset or not but he didn’t seem like it. Honestly, Dean didn’t deserve someone as patient as Cas. 

The two of them ordered pizza and put on a movie that Dean didn’t really pay attention to since he worked on his homework.

In bed, Dean normally took his time when he fucked Cas but that night Dean made it quick so he could go to bed. Exhaustion prevented him from making it anything else besides hot and rushed. Cas moaned his name and came before Dean.

 

 

To add to Dean’s stress, Sam said that their father drank more than usual. Dean had to worry about John being stupid and somehow hurting himself or Sam. 

“What the fuck is making him drink more?” Dean asked.

“I, uh, don’t know,” Sam replied.

Even though they spoke over the phone, Dean could tell Sam lied.

“Sam, tell me.”

“Okay, okay. He might have been drunk the other night and was just worried about us. You know, college for both of us and you and Cas…”

“What about me and Cas?” Dean snapped. 

Sam let out a sigh.

“He was just rambling about Mom, what she would say.”

“What she would say about me dating a guy?”

“I think so,” Sam answered.

“That’s bullshit,” Dean said, “I don’t care if he has a problem all of a sudden, she wouldn’t have cared. As long as I was happy.”

That’s what his dad said when he came out to him and said he and Cas were together. He just cared about Dean’s happiness. Apparently, he lied. 

“Are you?” Sam wanted to know.

Dean paused to answer. Classes were hard and work was demanding but he lived with someone he loved who loved him back. That was more important than the other crap.

“Yeah, Sam. I am.”

 

 

“Hey, Cas,” Dean said, awake first for once. 

Cas made a noise of recognition but didn’t open his eyes.

“I’m going to go home this weekend.”

One blue eye opened.

“Sam is worried about our dad’s drinking so I’m just going to check on them. You want to come with?” 

“Sure.”

“Great. Coffee?” Dean said with a smile.

Cas nodded. Dean kissed the top of his head before getting out of bed to get them a couple cups of coffee.

 

 

The two of them drove along to Dean’s house, Cas close to Dean in the long bench style front seat of the old Impala. Dean appreciated the company and extra warmth Cas provided in the February cold.

“Thanks for coming with, Cas.”

“Of course. I enjoy spending time with you and seeing Sam.”

Dean took a moment just to appreciate Cas snuggled up against him.

“I wish my dad still had my mom. I think that would make things easier for him.”

Cas nodded, not sure what else to say.

When they got to the Winchester house, the two of them let themselves in.

John sat at the kitchen table with the Friday paper and a glass of whiskey. 

“Dad?”

“Dean. Cas,” John replied, only kind of glancing at them.

“Why aren’t you at work?” Dean asked.

“Taking a day off,” John shrugged. 

“Isn’t a little early to be drinking?” Dean argued. 

The clock above the fridge read one in the afternoon. 

“Don’t come back home just to lecture me, son.”

Dean had an apology on his tongue out of habit but swallowed it. 

“I wouldn’t have to lecture if I wasn’t worried. Sam called, that’s why I’m here.”

“Oh, he did. Good for him. Doesn’t mean I can’t do what I want in my own damn house.”

“Dad…”

John threw the paper down and picked up his glass. Dean shifted enough to stand in front of Cas in case John felt like throwing the glass. It wouldn’t have been the first time. 

He stood. 

“Go back to school. Try to make your mother proud,” John said, turning a sour look towards Cas.

“You got something to say, say it,” Dean snarled, thinking about what Sam said on the phone. 

“I’ve got nothing to say. Why don’t you get out of here? You and your boyfriend.”

John practically spat the word boyfriend. He brushed against Dean as he went past into his room, slamming the door.

“God damn it,” Dean cursed, fingers pinching the bridge of his nose. 

Cas reached out and placed a reassuring hand on Dean’s shoulder. 

“We might as well just wait for Sam to come home. Want something to eat?” Dean offered.

“Uh, sure. But…”

“He won’t come out of there for a while.”

He added “stubborn jackass” under his breath. 

Dean and Cas sat down and had a couple of sandwiches and sodas. A couple of hours after they had arrived, Sam came home from school.

“Hey, Dean,” Sam grinned. “Hey, Cas.”

“Hi, Sammy,” Dean said, giving his brother a hug. 

“Hello, Sam,” Cas greeted.

The three of them sat on the couch.

“Dad in his room?” Sam asked.

“Yup. He was drinking when we showed up. Said he was taking the day off from work.”

“He lied. Dean, he got fired.”

“He tell you that?” Dean asked.

“No, but I know.” 

“Fuck,” Dean swore, dropping his head into his hands.

Cas rubbed his back reassuringly. 

“What are we going to do?” Sam asked.

The kid was sixteen and Dean hated that he had to deal with this shit. He should have focused on school and getting into college. Not his father’s drinking. 

“What the fuck are you still doing here?” John slurred. 

He seemed significantly more drunk than before and Dean figured he had another bottle of something in his room. Dean took the blame for letting the drinking worsen and letting Sam shoulder it alone.

“Dad, you need help,” Sam said.

He, Dean and Cas stood to face John.

“Don’t tell me what I need, boy.”

“Dad, seriously. You’re going to hurt yourself,” Dean pleaded.

“Your mother…”

Dean braced himself for the worst to come next. The man had no filter and all of his prejudices would come out.

“She wouldn’t have wanted this for you. I can’t even imagine what she would say,” John glared.

“Mom would have said the same thing you told me when I said I was dating Cas. That it only mattered that I was happy!” Dean said, yelling by the end.

John shook his head.

“I don’t have to listen to you. I don’t need this shit in my house.”

John walked out the front door.

Sam and Dean shared a look and Sam shrugged. At least he left on foot, if he…

The unmistakable sound of the Impala starting caused Dean’s stomach to sink. His hand went to the empty pocket of his jacket.

“When he bumped into me, he swiped the keys,” Dean explained.

He ran outside with Sam and Cas right behind him. 

“DAD!” Dean yelled. 

He struggled to start the car. Dean got to the driver’s side and begged his dad not to go.

“Please, get out of the car. Dad…”

John swung the door open into Dean’s face. He fell back from the impact and could feel the warm gush of blood from his likely broken nose. 

The Impala backed out of the driveway and swerved on down the road.

“Dean, are you okay?” Sam asked.

He and Cas crowded Dean, still on the ground. 

“I’m fine. We have to call the police,” Dean said.

“On Dad? Dean…”

Cas dialed. 

 

Cas got an ambulance for Dean to take care of his nose despite Dean’s pleas that he didn't need medical attention. He also protested that they couldn’t leave in case John came back. Cas told the police to find John before he hurt anyone.

The three of them got to the hospital emergency room. It didn’t take long to patch Dean up and he knew he would have to ice it after they set it. Dean had his nose broken before and he knew the drill. 

Dean’s cell phone rang. 

“Hello?”

“Dean Winchester?”

“Yes? Who’s this?”

“Officer Henriksen. We found your father.”


	6. Part 2 of What Happened Five Years Ago

**Summary for the Chapter:**

> Part two of what happened five years ago.

**Notes for the Chapter:**

> This is really the most angst-y chapter just a heads-up. The next chapter will be the last one.

PART TWO OF WHAT HAPPENED FIVE YEARS AGO

 

Henriksen, the officer in charge of finding John, told Dean they found his father. 

“Is he okay?” Dean asked, fearing the worst.

Sam and Cas looked at him with similarly concerned faces.

“I’m afraid he was in an accident,” Henriksen said. “He’s coming to you guys at the hospital.”

“Is he going to be okay? How bad is it?” Dean demanded to know.

“I…it’s not for me to say. The EMT’s and doctors will do their best.”

“Do their best? What the fuck…” Dean started to yell.

“I’m sorry, Dean.”

Henriksen hung up.

“Fuck,” Dean cursed.

“Is he okay?” Sam asked.

“I don’t know, Sam. He’s coming here.”

Ten minutes later, they wheeled John into the ER on an ambulance’s gurney. Dean’s stomach churned. He had never seen so much blood in his life. 

Cas grabbed his hand and squeezed it.

The three of them sat in the waiting room for what felt like days and became stiff and sore. Every time a doctor came out, their heads would snap up but it took an hour and a half until a doctor finally came to talk to them.

“Winchester?”

The three of them stood.

“Is he okay?” Dean asked.

“Are you family?” the doctor wanted to know.

“His son,” Dean snapped. “Is he okay?”

“It was a very serious car accident,” the doctor began. “We took him for surgery since he had a broken leg and a punctured lung from a broken rib. There was also severe bruising and lacerations all over his body. The worst, I’m afraid, was that his head was badly injured…”

“And?” Dean said impatiently.

“He’s in a coma.”

“When will he wake up?” Sam asked, eyes wide and scared.

“It’s more like ‘if’ at this point. I’m so sorry,” the doctor said regretfully.

“Was anyone else hurt?” Dean wanted to know, eyes squeezed shut.

“There was another car involved but they’re all in stable condition,” the doctor said before leaving.

Dean let out a small sigh of relief. He felt guilty enough that his dad drove because he let him get his keys and couldn’t stop him leaving. If anything happened to that other family…

“This isn’t your fault and they aren’t your responsibility,” Cas said, seeming to read Dean’s mind.

Dean nodded numbly, not letting his boyfriend’s words comfort him.

After another hour, they had John stabilized and in a room in the intensive care unit. The three of them said they were brothers so Cas could come with and went to see him. When it didn’t look like he would wake up anytime soon, they decided to go home and they took a taxi. Cas had to convince Dean to leave and his exhaustion won out.

At home in bed, Dean was the little spoon with Cas curled protectively behind him. Cas had even breathing and was sound asleep but not Dean.

The next morning, after only grabbing barely two hours of sleep, Dean looked like crap. Sam and Cas were nice enough not to say anything and they both looked well rested, or as well as could be expected. Cas had made a nice breakfast and forced the two brothers to eat. Sam didn’t complain and wolfed down his plate.

“Dean, you have to eat,” Cas insisted.

Too tired to argue, he took small bites of the bacon Cas put in front of him.

The three didn’t say much as they took a taxi back to the hospital. A long, boring Sunday of watching nurses and doctors come in and out of the room stretched on. John’s condition hadn't changed and his waking up was still a big maybe. 

“Dean, it’ll be okay,” Cas reassured Dean, kissing the knuckles of the hand he had been holding most of the day.

Dean didn’t say anything.

Cas used his other hand to lift Dean’s face to get him to look at him.

“I mean it,” Cas said. “Everything will be okay.”

The next day, Cas took a bus back to campus. As much as he wanted to be there for Dean, he had to go to class but didn’t bother suggesting Dean leave his father’s side and worried brother. Cas knew he wouldn't. 

After classes, Cas went back at the hospital and brought some take-out for them all to eat. It wasn’t healthy but they had to eat.

Dean called into work and explained his situation as well as e-mailing his professors. That gave him something to do for a brief moment to keep his mind distracted even for short time. Everyone was very understanding. 

The next day, Dean made Sam go to school and follow Cas’s example. 

“That’s not fair, who says I have to go and not you?” Sam asked.

“I’m twenty-one. You’re sixteen. The law does,” Dean sighed. 

He didn’t want to argue with his brother but John’s fuck-up wouldn't ruin his brother’s junior year. The kid had the ACT to take and needed to keep his grades up. For Dean, it was a long shot he even went to college in the first place. He didn’t matter, Sam did. 

Tuesday after the accident while Sam was at school, Cas sat with Dean since his classes were in the afternoon. 

“You can’t blame yourself,” Cas said.

“He shouldn’t have had the keys. I should have been home in the first place to know how bad it was, that isn’t on Sam’s shoulders,” Dean reasoned.

“Your father made some poor choices,” Cas said, treading lightly on the topic of John.

Dean tensed. 

“It doesn’t help to sit here day and night,” Cas tried.

“I have to be here when he wakes up,” Dean said, eyes set straight ahead.

Cas didn’t know what else to say. He knew Dean’s attendance had been solid and the two days he missed weren’t a problem but anymore and he would fall very far behind.

“Dean…”

Dean turned to look at Cas with hopeful eyes that seemed to be looking for the answers to his situation. Cas couldn’t do anything but be there for him.

“I support you no matter what.”

“Thanks, Cas.”

 

A month later, the doctors pressured Dean to pull the plug on John. He had no electrical activity and he was clinically brain dead.

“I can’t,” Dean argued. “He’s my father. What happens to us if he’s gone?”

The doctor just gave him a sympathetic look and left the room. 

Dean sat in the hard plastic chair in the room and dropped his head in his hands. 

“You stupid son of a bitch,” Dean cursed, knowing his father wouldn’t hear him.

Maybe if John wasn’t so stubborn and homophobic, he wouldn’t have done this. If Dean had stayed in the closest longer or just never told his dad about Cas… anything to have kept him from drinking and driving that night. 

 

A week later, John passed away without Dean making any decisions about his father’s fate. His body just couldn’t handle the trauma from the accident.

Dean called Sam at school and told him. Then, he called Cas. The two of them left their classes and came to the hospital. 

The next few days blended together. A lot of people who said they knew John came to the funeral. Bills from the hospital, cemetery and funeral home came and John’s measly life insurance policy barely covered part of the total.

Dean officially dropped out of school despite protests made by both Sam and Cas. He needed to work more at the garage and started looking for a second job. Sam kept excelling at school just like Dean knew he would and Dean kept him largely in the dark about their dire financial situation. The kid didn’t need to worry. 

Since Dean had been spending so much time at home, he felt like he never saw Cas anymore. Any free time Dean had from work and the job hunt was spent fixing up the Impala which John had nearly destroyed. 

On a night in early April, Dean spent the night with Cas in their apartment. They had barely kissed or even touched each other since the accident. Dean just had too much on his mind. 

The two of them were face to face in bed. 

“I don’t know what to do, Cas,” Dean admitted.

“You’ll figure it out,” Cas consoled, hand running up and down Dean’s arm soothingly. 

“These bills are too much and I think we have to sell the house,” Dean said, eyes shut in shame.

“Hey. Look at me,” Cas insisted.

Dean slowly opened his eyes.

“I will help you. If that means you sell the house and Sam moves here and I work to help out, then that’s what we do,” Cas said.

“What kind of life is that? Crammed into an apartment, struggling to get by. You need to focus on school, not work,” Dean pointed out.

“What I have to do is help the man I love,” Cas said, voice strong and sure.

Dean let out a content sigh.

“I love you, too,” Dean replied.

 

By the end of April, Dean had a plan. The job hunt looked bleak and he had to sell the house to finish paying the bills John left behind. He fixed the Impala but the cost ran high. The only thing he could think to do was to move to South Dakota with an old friend of their dad’s, Bobby Singer. 

In South Dakota, they could live with Bobby and he would work with him fixing cars. Sam could do his senior year there before going to college. They would impose on Bobby for only a little bit. 

He didn't know how to tell Sam and Cas his plan. Sam liked Bobby and would go with Dean but Cas might be less understanding. Dean and Sam couldn’t be his problem and certainly couldn’t take his charity and mooch for an unknown period of time until Dean got his shit together. 

On Dean’s one day off during the week, he sat Sam down when he got home from school. 

“So, I haven’t really been totally upfront with you about what’s been going on since… Dad…”

“What’s wrong?” Sam asked, knowing Dean struggled to talk about their father’s death.

“We have to sell the house,” Dean said, finding it hard to look his brother in the eye.

Dean had to sell the house they grew up in, that their mother loved and wanted them to have a life in. He felt like he had failed his parents and Sam because he couldn’t keep it.

“And go where?” Sam asked.

“South Dakota, with Bobby. I already called him…”

“What about school?”

“We’ll move when the year is over,” Dean explained. “Then you can do senior year there.”

Sam took a pause to take it all in. 

“What about Cas?” Sam asked. “What did he say?”

“I…”

Dean ran a hand through his hair and stopped to squeeze the back of his neck. 

“I haven’t told him.”

“What are you going to say?”

“I don’t know, Sam.”

 

Dean was running out of time.

The school year was coming to an end and then he and Sam had to move. They slowly packed up the house and Dean still hadn’t told his boyfriend he had to go.

When he didn't pack or work, he spent time at the apartment with Cas. 

One morning, before they had to get up, Dean surprised Cas by waking him up with a blowjob.

After they had showered and brushed their teeth, Cas smiled at him over breakfast.

“That was unexpected,” Cas said, still smiling.

“Yeah, I, it had been… a while. I missed that,” Dean smiled back.

He could feel the smile not reach his eyes but it didn’t look like Cas took note. Dean would miss waking up with Cas, blowjobs or not. Just holding him… kissing him…

“Dean,” Cas said, bringing him back.

“What?” Dean asked, eyes snapping up.

“Did you hear me?” Cas asked. “I made us a dinner reservation for tonight.”

“Oh, okay,” Dean grinned, taking Cas’s hand across their table. “Awesome.”

 

At home, Dean panicked. Their move was in a week and Cas had no idea. Dean couldn't keep dragging Cas into his shit. Cas had seen John before he nearly killed a family and saw Dean drop out and struggle in every sense of the word. He didn't take John’s death well. 

If anything, this just proved they didn’t belong together. Cas would be successful and rich and Dean would fix cars for the rest of his life. He couldn’t hold Cas back like that.

“Do you really want to drop a bomb on him like this at dinner?” Sam questioned.

“I don’t have a choice, Sammy,” Dean shrugged, buttoning his one shirt with buttons that wasn’t flannel.

 

Since the restaurant was in between the apartment and Winchester house, they decided to meet there. Cas, Dean figured, was hoping Dean would come home to the apartment after their date but Dean knew Cas wouldn’t want that after he told him the truth. 

“Hey, Cas,” Dean said, meeting him at the table.

“Hello, Dean.”

Cas stood to greet him and gave him a quick kiss before they sat back down. Dean took a deep breath and tried to store that memory since he feared that might be their last kiss.

For most of the meal, their conversation was normal. Cas told him about his classes and how a professor thought he had a real future in teaching. He asked Dean about work and Sam. 

During the main course, when they were almost done, Dean couldn’t wait any longer. Cas had finished his meal long before but Dean didn’t really have an appetite.

“Cas…”

“Dean…”

They said each other’s names at the same and laughed a little. Cas insisted Dean go ahead.

“So, you know things haven’t been easy since…”

“I understand,” Cas said.

“The bills have been too much and the house has been on the market for a while now and I couldn’t figure out how to tell you.”

“There’s more than you just selling the house,” Cas said, always perceptive.

Dean glanced around the restaurant before looking down at the steak he had only eaten half of. 

“Sam and I have to move,” Dean pointed out.

“Of course,” Cas agreed. “I wanted to say, we could all look for something between the university and Sam’s school. A house, for all of us.”

Dean could only stare. His boyfriend had considered everything it seemed. Dean couldn’t expect Cas to deal with his self-pity and pathetic shit forever. The man across from him seemed so excited and Dean hated to destroy him.

“You seem… confused,” Cas observed, eyebrows knit together. “Like that idea is implausible.”

“I…Sam and I were going to go to South Dakota. There’s a family friend, Bobby…”

“South Dakota,” Cas said, deadpan.

Dean knew that voice, the steady calm before the storm. 

“I have been the absolute worst boyfriend the last couple of months and it wouldn’t get easier, Cas. It would get worse. And you deserve better, so much better and I can’t…”

“There is no one better or different that I would ever want, Dean,” Cas said, his face fallen.

“I can’t give you the life you deserve, Cas,” Dean tried to explain.

“You don’t have to give me a life,” Cas said, tears appearing in his eyes. “Just be in it!”

“I’m no good for you, Cas. I drink too much, I panic when things get too real. I’m sorry,” Dean said, voice a hoarse whisper. "This is over." 

“No, you can’t do this. I was going to… we were…” Cas said, unable to voice his thoughts. 

Dean stood, one tear falling down his face.

“I’m sorry,” he repeated.

“Dean, I love you. Don’t do this,” Cas pleaded.

“I love you, too. That’s why I have to.”

Dean turned around to look at Cas when he got to the door. He looked down and his shoulders shook, sobbing and absolutely crushed. Dean wished he hadn’t glanced back, that final look a haunting memory of how he fucked up.

Cas sat at the table and took a small, velvet box out of his pocket. If the ring inside didn’t mean so much to him, he would have thrown it across the restaurant.


	7. Big Finale

DAY AFTER THE COFFEE SHOP

 

Dean turned his phone over and over in his hand while pacing in his apartment. Calling Cas while sober made his stomach twist but the idea of not calling him made his heart sink. They needed to talk even if he had every right to ignore Dean forever.

After five years, the guilt of up and running to South Dakota and then the shitshow in the coffee shop burned at Dean and he needed to make this right. 

He pressed call.

“Dean?” Cas asked on the other line.

“Cas, I…”

“Are you drunk again? It’s not even four.”

“No,” Dean interrupted. “Stone cold sober. I need to be for what I have to say and I owe you that much at least.”

Dean couldn’t gauge how Cas felt since he kept quiet and waited for Dean to continue so he let out a deep breath and went on. 

“I didn’t know Sam was planning that and I’m sorry. I’m sorry for a lot of things really, that’s just the beginning. Do you have a moment? This could take a while.”

“I’m on a break at my conference,” Cas said so Dean took that as a yes.

“I’m sorry I ran. I’m sorry I didn’t trust you or let you in. I’m sorry I’m such an idiot. I’m sorry I called all the time saying stupid stuff. Cas, you were the best thing to ever happen to me and I threw it away because I was scared. I shouldn’t have walked out of that restaurant five years ago and I shouldn’t have let you walk away yesterday without chasing you.”

Cas didn’t say anything but Dean could still hear him on the other line. 

“And I’m sorry for bothering you now,” Dean said.

He figured Cas had to go back to his conference and almost hung up.

“Dean, maybe we should talk about this in person,” Cas suggested.

Dean knew he deserved less. 

“If, uh, yeah if you want to. Sure,” Dean managed. 

“Dinner?” Cas offered.

“Absolutely,” Dean agreed. “Wherever you want, just name it.”

They made plans before Cas had to get back to his conference.

Dean checked the time. He had three hours to kill and spent a good amount of time pacing anxiously around his apartment. 

To pass the time, he gave his brother a call.

Sam didn’t answer so Dean left a voicemail.

“Look, I’m still royally pissed and owe you a serious beatdown because what the fuck, man. But, me and Cas are meeting for dinner to talk because the coffee shop didn’t go well and he’s giving me a millionth chance here. I’m going to try my hardest not to mess this up and I’ll let you know how it goes. Even though you’re a bitch.”

He aimlessly flipped through channels then took an excessively long shower, letting the hot water relax him marginally. Dean, like so many times before, imagined them getting back together but knew that was a longshot. But he couldn’t help his dreaming no matter how lofty and ridiculous. If, by some miracle, Cas wanted him again he would not make the same mistake again by letting that man get away. Not a second time. 

He paired a nice Henley with his good jeans and left.

The restaurant they met at felt oddly similar to the one they broke up at five years ago. It was fancy, better than Dean’s usual, and decorated in a similar fashion. It had fountains and tanks with the lobsters that would soon be dinner and ornate chandeliers and staircases.

“Hello, Dean,” Cas greeted.

He wore a white dress shirt and black pants and looked good. 

“Hey, Cas,” Dean replied. “I didn’t know there was such a nice place around here.”

The two of them sat.

“Did you want to start? Tell me how much I fucked up, how I should leave you alone? Give you a turn to leave me alone at dinner?” Dean began, not wanting to waste time with small talk like the day before. 

“Honestly, I wanted that for years. I wanted to hate you, Dean. But I couldn’t,” Cas responded, giving Dean his most sincere look.

“I wouldn’t blame you if you did,” Dean said quietly and looked down.

“Well, your apology earlier helped,” Cas joked.

The joke took Dean by surprise and he couldn’t help but laugh.

“Dean, do you want to know what your problem is?” Cas asked gently.

“Sure,” Dean answered, one side of his mouth turned up in a bemused smile as he met Cas’s eyes.

He really did want to hear what Cas thought, it could be a conversation to last them to dessert. 

“Your problem is that no one hates you as much as you hate you.”

Cas paused and let Dean take that in as they ordered their meals, neither really caring what they actually ordered. They both stuck to water. Dean never touched a drop of alcohol if he knew he had to drive, not after what happened to John. 

“You carry this guilt and self-hate and loathing,” Cas continued, “and you don’t need to. You are amazing and I know you thought you were doing the right thing when you left even though it took me a long time to see it.”

“I…What?” Dean asked. “I’m sorry, I’m still having a hard time grasping the fact that you don’t hate me. You should.”

“No, I shouldn’t,” Cas said. 

The two took a moment and just drank their water.

“Those nights I called, you were all I could think about even if I was drunk. I really missed you, Cas.”

“I missed you, too. You know, I didn’t let you go easily. I went to your house a lot after you left to try to talk to you.”

“Yeah, I kind of bumped up the move. I thought it would be easier to just go.”

Cas’s gaze softened even more.

“I was going to propose that night at the restaurant,” Cas said.

“You…what? Really?” Dean asked, eyes wide at that dropped bomb. 

He never knew that. God, he was so stupid. 

“If I had stayed…” he continued, mind working in overdrive of all the possibilities.

“Things could have been a lot different to say the least,” Cas said with a small smile.

“Holy shit,” Dean cursed.

They paused again, taking everything in. 

“When you started calling, I was pissed again,” Cas admitted. “I was so close to getting over you and you came storming back into my life and then I started questioning everything.”

“Like what?”

“My engagement for one,” Cas answered.

“Oh,” Dean said in a small voice. He had kind of forgotten about that. 

“When Sam called, I knew I would have to see you. Even if he hadn’t planned anything or reached out to me, I would have found him to ask about how to find you. I couldn’t have come down here without trying.”

They were interrupted as their food came. Dean got a trio of filet medallions with parmesan on top and potatoes while Cas got tilapia with wild rice. 

“I called off my engagement,” Cas said.

Dean nearly choked on his food. 

“Why?” Dean asked in disbelief. 

“I couldn’t marry someone when there was someone I loved more,” Cas explained like it was simple and obvious. 

“Me?” 

“Of course,” Cas said, face splitting in a huge grin that showed his gums. “Despite you being drunk, I did look forward to your calls and hearing your voice. I just didn’t know how to call back the next day.”

“Well, shit,” Dean smiled back.

The rest of their meal went better than Dean could have hoped and his cheeks hurt from smiling and laughing so much. 

 

FIVE MONTHS LATER

 

“You’re fine, Dean. Everything will be fine,” Sam said, both hands on his brother’s shoulders. 

“I know, I know,” Dean answered. “I’m just freaking out. I shouldn’t because it’s Cas but dude. A wedding? Me? It just never really was something I pictured. Well, except with him.”

“Exactly. You two will be so happy and you’ll realize how silly you’re being. Deep breath.”

Dean inhaled and let it out shakily.

“Better?” Sam asked.

Dean shook his head. Sam just gave him a look.

“As your best man, I’m telling you to get it together,” Sam said. “Don’t leave the man you love waiting too long, okay? I’ll see you out there.”

Sam left Dean alone in the room. 

Dean and Cas spent the last five months getting to know each other again. The distance was hard at first but Cas moved to California and started looking for a new teaching opportunity while he did his research and writing. Dean got a promotion at the firehouse and Jess was about to have his niece. Cas also wasn’t too keen on living in the same city as his ex-fiance.

It seemed like no time had passed at all. They still felt like their bond was unbreakable and they easily fell back into a routine with each other. 

Cas reassured Dean he forgave him for leaving and Dean reassured Cas that he was never going anywhere ever again. 

At the restaurant where they had reconciled, Cas got his chance to propose and Dean got his chance to say yes. That was a month and a half ago but they weren’t wasting any more time. Five years had already been wasted. 

Dean smiled thinking about lucky he was to have Cas again. He had gotten his head out of his ass and they had their whole lives ahead of them.

He walked out and met Cas at the end of the aisle so they could walk down together. Sam was waiting at the end of the aisle along with the one brother Cas liked, Gabriel. Sam was lucky enough to be promoted as well since Lucifer was part of a federal investigation involving fraud and tampering with evidence and juries.

“Damn, you look good,” Dean said, eyeing his very soon-to-be husband up and down.

“I was going to say the same thing,” Cas said.

“I’m so lucky. God, I can’t believe I’m marrying the most amazing man ever.”

“No, I’m pretty sure that’s what I’m doing,” Cas said with a smile. 

“I love you, Cas,” Dean said, lacing their fingers together. 

“I love you too, Dean,” Cas returned, giving Dean’s hand a little squeeze. “Ready?”

Dean nodded and they walked down the aisle.


End file.
